US5288427A - Electrooptical display element - Google Patents
Electrooptical display element Download PDFInfo
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- US5288427A US5288427A US07/815,832 US81583291A US5288427A US 5288427 A US5288427 A US 5288427A US 81583291 A US81583291 A US 81583291A US 5288427 A US5288427 A US 5288427A
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- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 31
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 25
- 125000001140 1,4-phenylene group Chemical class [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims abstract description 20
- 125000005407 trans-1,4-cyclohexylene group Chemical group [H]C1([H])C([H])([H])[C@]([H])([*:2])C([H])([H])C([H])([H])[C@@]1([H])[*:1] 0.000 claims abstract description 20
- 238000004904 shortening Methods 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 125000001589 carboacyl group Chemical group 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 230000007704 transition Effects 0.000 claims description 3
- 101150108015 STR6 gene Proteins 0.000 claims 1
- 239000003989 dielectric material Substances 0.000 abstract description 11
- 125000004430 oxygen atom Chemical group O* 0.000 abstract description 6
- 239000000203 mixture Substances 0.000 description 41
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Substances N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 35
- OXBRRUNAAVNTOZ-SHTZXODSSA-N C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1C1=CC=C(OCC)C=C1 OXBRRUNAAVNTOZ-SHTZXODSSA-N 0.000 description 28
- MDUQZBFHDPNORI-HDJSIYSDSA-N CCC[C@H]1CC[C@@H](CC1)c1ccc(OC)cc1 Chemical compound CCC[C@H]1CC[C@@H](CC1)c1ccc(OC)cc1 MDUQZBFHDPNORI-HDJSIYSDSA-N 0.000 description 28
- -1 tetrabutylammonium tetraphenylborate Chemical compound 0.000 description 28
- BPVJENLMEMWFBW-QAQDUYKDSA-N CCCCOc1ccc(cc1)[C@H]1CC[C@H](CCC)CC1 Chemical compound CCCCOc1ccc(cc1)[C@H]1CC[C@H](CCC)CC1 BPVJENLMEMWFBW-QAQDUYKDSA-N 0.000 description 26
- LUCHFKBTWHPREI-UHFFFAOYSA-N 1-(4-propylcyclohexyl)-4-[4-(4-propylcyclohexyl)phenyl]benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C2CCC(CCC)CC2)C=C1 LUCHFKBTWHPREI-UHFFFAOYSA-N 0.000 description 23
- PJBOOKMLDPERRS-PCYFZWJMSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C=C1 Chemical group C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C=2C=CC(=CC=2)[C@@H]2CC[C@@H](CCC)CC2)C=C1 PJBOOKMLDPERRS-PCYFZWJMSA-N 0.000 description 22
- NBOMAZVNDYECTP-DANJKSSVSA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)[C@H]1CC[C@H](CCCCC)CC1 Chemical group CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1)[C@H]1CC[C@H](CCCCC)CC1 NBOMAZVNDYECTP-DANJKSSVSA-N 0.000 description 18
- 230000002349 favourable effect Effects 0.000 description 18
- RDPCRVRASQOZBX-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 4-propylbenzoate Chemical compound C1=CC(CCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 RDPCRVRASQOZBX-UHFFFAOYSA-N 0.000 description 12
- ISGYBTOINXAQJG-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 4-pentylbenzoate Chemical compound C1=CC(CCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 ISGYBTOINXAQJG-UHFFFAOYSA-N 0.000 description 11
- DLLIPJSMDJCZRF-UHFFFAOYSA-N 4-(4-ethylphenyl)benzonitrile Chemical group C1=CC(CC)=CC=C1C1=CC=C(C#N)C=C1 DLLIPJSMDJCZRF-UHFFFAOYSA-N 0.000 description 10
- RVLAXPQGTRTHEV-XYPYZODXSA-N CCCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCCC[C@H]1CC[C@H](C(O)=O)CC1 RVLAXPQGTRTHEV-XYPYZODXSA-N 0.000 description 10
- BALGERHMIXFENA-MGCOHNPYSA-N CCCC[C@H]1CC[C@H](C(O)=O)CC1 Chemical compound CCCC[C@H]1CC[C@H](C(O)=O)CC1 BALGERHMIXFENA-MGCOHNPYSA-N 0.000 description 10
- XFMPTZWVMVMELB-UHFFFAOYSA-N 4-(4-propylphenyl)benzonitrile Chemical group C1=CC(CCC)=CC=C1C1=CC=C(C#N)C=C1 XFMPTZWVMVMELB-UHFFFAOYSA-N 0.000 description 9
- BJTUQNRKEMWBHS-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 4-heptylbenzoate Chemical compound C1=CC(CCCCCCC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 BJTUQNRKEMWBHS-UHFFFAOYSA-N 0.000 description 8
- JHDGZPSFHYZDNF-GUJRETQESA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCC JHDGZPSFHYZDNF-GUJRETQESA-N 0.000 description 8
- QDZHKLQGOIWETL-QWZLJSJVSA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCCCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCCCC QDZHKLQGOIWETL-QWZLJSJVSA-N 0.000 description 8
- UZSKJVZYSFNTSE-ZWGSZDQZSA-N C(CCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCC UZSKJVZYSFNTSE-ZWGSZDQZSA-N 0.000 description 8
- VRDNRAMDWPJGBD-MVBYDDMTSA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC VRDNRAMDWPJGBD-MVBYDDMTSA-N 0.000 description 7
- RRYWSYNNAXXFJF-MVBYDDMTSA-N C(CCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCCCC Chemical compound C(CCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)C(=O)OC1=CC=C(C=C1)CCCCC RRYWSYNNAXXFJF-MVBYDDMTSA-N 0.000 description 7
- DEWAVJLSNXMVGF-FUMLSLJBSA-N C(CCCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCC DEWAVJLSNXMVGF-FUMLSLJBSA-N 0.000 description 6
- SYCNHFWYTQQMNG-UHFFFAOYSA-N 2-fluoro-4-(4-pentylcyclohexyl)-1-[4-(4-propylcyclohexyl)phenyl]benzene Chemical group C1CC(CCCCC)CCC1C1=CC=C(C=2C=CC(=CC=2)C2CCC(CCC)CC2)C(F)=C1 SYCNHFWYTQQMNG-UHFFFAOYSA-N 0.000 description 5
- SRJLZDPWUSOULH-UHFFFAOYSA-N 2-fluoro-4-(4-propylcyclohexyl)-1-[4-(4-propylcyclohexyl)phenyl]benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C=2C(=CC(=CC=2)C2CCC(CCC)CC2)F)C=C1 SRJLZDPWUSOULH-UHFFFAOYSA-N 0.000 description 5
- 239000004305 biphenyl Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CDXMJQJMSJCJLU-UHFFFAOYSA-N (4-cyano-3-fluorophenyl) 4-ethylbenzoate Chemical compound C1=CC(CC)=CC=C1C(=O)OC1=CC=C(C#N)C(F)=C1 CDXMJQJMSJCJLU-UHFFFAOYSA-N 0.000 description 4
- MMWGNKDKZYGDKH-WKILWMFISA-N C(C)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(C)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC MMWGNKDKZYGDKH-WKILWMFISA-N 0.000 description 4
- YZEXUPSVZPXFON-WKILWMFISA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(OC)cc1 Chemical compound CCCCC[C@H]1CC[C@@H](CC1)c1ccc(OC)cc1 YZEXUPSVZPXFON-WKILWMFISA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000004973 liquid crystal related substance Substances 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 230000003068 static effect Effects 0.000 description 4
- JHWDKPIJNPJWBS-WGSAOQKQSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C(=O)OC=2C=C(F)C(C#N)=CC=2)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(C(=O)OC=2C=C(F)C(C#N)=CC=2)C=C1 JHWDKPIJNPJWBS-WGSAOQKQSA-N 0.000 description 3
- WODHCUQSMMCWJW-QAQDUYKDSA-N CCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(=O)Oc1ccc(C#N)c(F)c1 Chemical compound CCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)C(=O)Oc1ccc(C#N)c(F)c1 WODHCUQSMMCWJW-QAQDUYKDSA-N 0.000 description 3
- DOALOUQODWWGEZ-UHFFFAOYSA-N 1-ethyl-4-[4-(4-propylcyclohexyl)phenyl]benzene Chemical group C1CC(CCC)CCC1C1=CC=C(C=2C=CC(CC)=CC=2)C=C1 DOALOUQODWWGEZ-UHFFFAOYSA-N 0.000 description 2
- 125000005449 2-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:2])C([H])=C(F)C([*:1])=C1[H] 0.000 description 2
- 239000005247 4-Ethyl-4'-(trans-4-propylcyclohexyl)biphenyl Substances 0.000 description 2
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 2
- GJHKWLSRHNWTAN-QAQDUYKDSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(OCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(OCC)C=C1 GJHKWLSRHNWTAN-QAQDUYKDSA-N 0.000 description 2
- RXNHJSWEUSIGAN-VVPTUSLJSA-N C1C[C@@H](CCCCC)CC[C@@H]1CC[C@@H]1CC[C@@H](C(O)=O)CC1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1CC[C@@H]1CC[C@@H](C(O)=O)CC1 RXNHJSWEUSIGAN-VVPTUSLJSA-N 0.000 description 2
- TYXZVPMEKLRAGX-OEOGMAASSA-N CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1F)[C@H]1CC[C@H](CCCCC)CC1 Chemical group CCCCC[C@H]1CC[C@@H](CC1)c1ccc(cc1)-c1ccc(cc1F)[C@H]1CC[C@H](CCCCC)CC1 TYXZVPMEKLRAGX-OEOGMAASSA-N 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- VLKZOEOYAKHREP-UHFFFAOYSA-N methyl pentane Natural products CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 125000005451 3-fluoro-1,4-phenylene group Chemical group [H]C1=C([*:1])C([H])=C(F)C([*:2])=C1[H] 0.000 description 1
- PJPLBHHDTUICNN-UHFFFAOYSA-N 4-(4-butylphenyl)benzonitrile Chemical group C1=CC(CCCC)=CC=C1C1=CC=C(C#N)C=C1 PJPLBHHDTUICNN-UHFFFAOYSA-N 0.000 description 1
- 239000005209 4-Butyl-4'-cyanobiphenyl Substances 0.000 description 1
- PZUUMRKZMNIXKL-CYWFSMGFSA-N C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCCCC Chemical compound C(CC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)CCCCC PZUUMRKZMNIXKL-CYWFSMGFSA-N 0.000 description 1
- JTSARQMEFWLSHO-IYARVYRRSA-N C(CCC)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC Chemical compound C(CCC)OC1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)CCCC JTSARQMEFWLSHO-IYARVYRRSA-N 0.000 description 1
- VPVTYGYNGKPWBV-YHVNJZMGSA-N C(CCCC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)[C@@H]1OC[C@H](CO1)[C@@H]1CC[C@H](CC1)CCCCC Chemical compound C(CCCC)C1=CC=C(C=C1)[C@@H]1CC[C@H](CC1)[C@@H]1OC[C@H](CO1)[C@@H]1CC[C@H](CC1)CCCCC VPVTYGYNGKPWBV-YHVNJZMGSA-N 0.000 description 1
- WWWFKDNGTNPGOZ-ZKHCSVRISA-N C(CCCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)OC Chemical compound C(CCCC)[C@@H]1CC[C@H](CC1)[C@@H]1CC[C@H](CC1)CCC1=CC=C(C=C1)OC WWWFKDNGTNPGOZ-ZKHCSVRISA-N 0.000 description 1
- GZMMUVKMQPSLLS-YSXIEMCBSA-N C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC=CC=2)CC1 Chemical compound C1C[C@@H](CCC)CC[C@@H]1[C@@H]1CC[C@@H](C=2C=CC=CC=2)CC1 GZMMUVKMQPSLLS-YSXIEMCBSA-N 0.000 description 1
- RXBBPIPXHBOXOU-KESTWPANSA-N C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 Chemical compound C1C[C@@H](CCCCC)CC[C@@H]1C1=CC=C(CCC)C=C1 RXBBPIPXHBOXOU-KESTWPANSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 101100386054 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) CYS3 gene Proteins 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 230000003098 cholesteric effect Effects 0.000 description 1
- 150000003983 crown ethers Chemical class 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- RBBNOVKRLWDEGC-UHFFFAOYSA-M dodecyl-ethyl-dimethylazanium;4-hexoxybenzoate Chemical compound CCCCCCOC1=CC=C(C([O-])=O)C=C1.CCCCCCCCCCCC[N+](C)(C)CC RBBNOVKRLWDEGC-UHFFFAOYSA-M 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000011835 investigation Methods 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000002310 reflectometry Methods 0.000 description 1
- 101150035983 str1 gene Proteins 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3001—Cyclohexane rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/08—Non-steroidal liquid crystal compounds containing at least two non-condensed rings
- C09K19/30—Non-steroidal liquid crystal compounds containing at least two non-condensed rings containing saturated or unsaturated non-aromatic rings, e.g. cyclohexane rings
- C09K19/3098—Unsaturated non-aromatic rings, e.g. cyclohexene rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3491—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having sulfur as hetero atom
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
- C09K19/06—Non-steroidal liquid crystal compounds
- C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
- C09K19/3402—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom
- C09K2019/3422—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having oxygen as hetero atom the heterocyclic ring being a six-membered ring
Definitions
- the invention relates to electrooptical liquid-crystal display elements (LC display elements) based on TN cells having a particularly short switch-on time T on when switched from a first voltage below or approximately at the threshold voltage to a second voltage which is on the increase of the electrooptical characteristic line.
- the invention is thus of particular importance in high-multiplex LC display elements and in particular in TFT-addressed LC display elements having a particularly short switch-on time.
- nematic or nematic cholesteric liquid-crystalline materials to modify their optical properties, such as light absorption, light scattering, birefringence, reflectivity or color are utilized.
- the function of display elements of this type is based, for example, on the phenomena of dynamic scattering and the deformation of allied phases, on the guest-host effect, the Schadt-Helfrich effect in the twisted cell, the SBE effect or the cholesteric-nematic phase transition.
- LC phases are required which must satisfy a large number of requirements. Particularly, important here are the chemical resistance to moisture, air and physical influences, such as heat, radiation in the infra-red, visible and ultra-violet region and electrical direct current and alternating current fields. Furthermore, a liquid-crystalline mesophase in a suitable temperature range, low viscosity, an optical anisotropy matched to the layer thickness, low temperature dependence of the threshold voltage, steep gradients of the electrooptical characteristic line and adequate dissolution capacity for pleochroic dyes are required of LC phases which can be used industrially.
- electrooptical liquid-crystal display elements An essential distinction is made in electrooptical liquid-crystal display elements between static drive and multiplex drive.
- electrooptical liquid-crystal display elements which are driven in "multiplex operation the voltage is switched from a first voltage V (off) to a second voltage V (on) and back. The ratio between these two voltages is determined by the "multiplex ratio" and the "bias". The absolute values for the two voltages are given by the operating voltage.
- V(on):V(off) ratio is 1.73.
- V(on) is 1.73 volts and V(off) is 1.00 volt.
- the V(on):V(off) ratio is, for example, 1.29; at an operating voltage of 5 volts, V(on) is 1.58 volts and V(off) is 1.22 volts.
- the second voltage V(on) is then on the increase of the characteristic line above the threshold voltage.
- the brightness is necessary for the brightness to be varied as desired in the range from, for example, 10% of maximum brightness up to, for example, 90% of maximum brightness by switching the voltage.
- the voltage is switched from below or in the region of the threshold voltage to a second voltage above the threshold voltage in the region of the increase in the characteristic line.
- the invention has the object of providing LC display elements which have a broad operating temperature range and only have the abovementioned disadvantages to a lesser extent, or not at all.
- LC display elements having particularly favorable electrooptical properties, in particular having extremely short switch-on times T on when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, are obtained when the dielectric contains at least one component of the formula I
- R 1 and R 2 independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--, where two O atoms are not linked directly to one another, or one of the two groups R 1 and R 2 is alternatively H,
- Z 1 is --CH 2 --O--, --OCH 2 --, --CH 2 CH 2 -- or a single bond
- a 1 is trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH 2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
- A is unsubstituted or fluorine-substituted 1,4-phenylene.
- the invention thus relates to a LC display element containing a liquid-crystalline phase described above, in particular an electrooptical display element based on a TN cell having a particularly short switch-on time T on when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, characterized in that the dielectric simultaneously contains at least one component of the formula I
- R 1 and R 2 independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--, where two O atoms are not linked directly to one another, or one of the two groups R 1 and R 2 is alternatively H,
- Z 1 is --CH 2 --O--, --OCH 2 --, --CH 2 CH 2 -- or a single bond
- a 1 is trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH 2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and is unsubstituted or fluorine-substituted 1,4-phenylene,
- R 3 is H or alkyl having 1 to 9 C atoms, in which, in addition, one or two nonadjacent CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--,
- R 4 is H, alkyl having 1 to 9 C atoms in which, in addition, one or two nonadjacent CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--, halogen, CN, NCS or N 3 ,
- Z 2 and Z 3 are each --CH 2 CH 2 --, --OCH 2 --, --CH 2 O-- --O--CO--, --CO--O--, or a single bond,
- a 2 and A 3 are each trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH 2 groups may be replaced by O and/or S,
- A' is unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N.
- the invention furthermore relates to an appropriate display element whose dielectric additionally contains at least one component of the formula IV
- Z 4 and Z 5 are each --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --O--CO--, --CO--O-- or a single bond,
- a 4 and A 5 are each trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
- n 0 or 1
- R 3 , R 4 , A 2 , A 3 , A, Z 2 and Z 3 have the meaning given in claim 4, and an appropriate electrooptical display element which is operated in the region of the first transmission minimum according to Gooch-Tarry.
- the invention furthermore relates to the use of compounds of the formula I
- R 1 and R 2 independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--, where two O atoms are not linked directly to one another, or one of the two groups R 1 and R 2 is alternatively H,
- Z 1 is --CH 2 --O--, --OCH 2 --, --CH 2 CH 2 -- or a single bond
- a 1 is trans-1,4-cyclohexylene in which, in addition one or two nonadjacent CH 2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
- A is unsubstituted or fluorine-substituted 1,4-phenylene
- liquid-crystalline dielectrics containing at least three liquid-crystalline compounds for shortening the switch-on time T on of electrooptical display elements based on a TN cell when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, and to a process for shortening the switch-on time T on of electrooptical display elements based on a TN cell when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, characterized in that the dielectric contains at least one component of the formula I
- R 1 and R 2 independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--, where two O atoms are not linked directly to one another, or one of the two groups R 1 and R 2 is alternatively H,
- Z 1 is --CH 2 --O--, --OCH 2 --, --CH 2 CH 2 -- or a single bond
- a 1 is trans-1,4-cyclohexylene in which, in addition one or two nonadjacent CH 2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
- A is unsubstituted or fluorine-substituted 1,4-phenylene.
- the invention finally relates to a dielectric for use in an electrooptical display element based on a TN cell having a particularly short switch-on time T on when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, characterized in that it simultaneously contains one component of the formula I
- R 1 and R 2 independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--, where two O atoms are not linked directly to one another, or one of the two groups R 1 and R 2 is alternatively H,
- Z 1 is --CH 2 --O--, --OCH 2 --, --CH 2 CH 2 -- or a single bond
- a 1 is trans-1,4-cyclohexylene in which, in addition one or two nonadjacent CH 2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
- A is unsubstituted or fluorine-substituted 1,4-phenylene, and at least one component selected from the compounds of the formulae II and III
- R 3 is H or alkyl having 1 to 9 C atoms, in which, in addition, one or two nonadjacent CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--,
- R 4 is H, alkyl having 1 to 9 C atoms in which, in addition, one or two nonadjacent CH 2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH ⁇ CH--, halogen, CN, NCS or N 3 ,
- Z 2 and Z 3 are each --CH 2 CH 2 --, --OCH 2 --, --CH 2 O-- --O--CO--, --CO--O--, or a single bond,
- a 2 and A 3 are each trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH 2 groups may be replaced by O and/or S,
- A' is unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
- Z 4 and Z 5 are each --CH 2 CH 2 --, --OCH 2 --, --CH 2 O--, --O--CO--, --CO--O-- or a single bond,
- a 4 and A 5 are each trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
- n 0 or 1
- R 3 , R 4 , A 2 , A 3 , A, Z 2 and Z 3 have the meaning given in claim 4.
- the dielectrics may also contain further additives known to those skilled in the art and described in the literature.
- furthermore conductive salts for example ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (compare, for example, Haller et al., Mol. Cryst. Liq. Cryst. Volume 24, pages 249-258, (1973)) for improving the conductivity, or substances for modifying the dielectric anisotropy, the viscosity and/or the orientation of the nematic phases can be added.
- Such substances are described, for example, in DE-OS 2,209,127, 2,240,864, 2,321,632, 2,338,281, 2,450,088, 2,637,430 and 2,853,728.
- the dielectrics according to the invention in particular the combination of components of the formulae I and II and/or III, have significantly shorter switching times (in particular significantly shorter switch-on times) under the specific drive conditions mentioned (that is to say, for example, in TFT or high-multiplex displays) than other dielectrics without this specific substance combination, even if relevant physical properties and measurement conditions (rotational viscosity, elastic constants, the product d ⁇ n of the layer thickness and the optical anisotropy, and the drive voltage) are virtually identical.
- the better switching (switch-on) times of the LC display elements according to the invention are caused not only by better viscosities or more suitable elastic constants. The reason is very probably above all the type of interactions between the LC molecules and the display surfaces. In particular, it can be assumed that the mixtures according to the invention have a greater tilt angle than other comparable mixtures and the switch-on time especially is therefore significantly shorter.
- R 1 and R 2 are, independently of one another, preferably alkyl in which, in addition, a CH 2 group (which is not linked directly to --O-- or --A 1 --) may be replaced by --O-- or --CH ⁇ CH--.
- Straight-chain alkyl groups having 1 to 5 C atoms are particularly preferred.
- Compounds of the formula I in which R 2 is alkanoyl are furthermore preferred.
- R 2 is then preferably straight-chain alkanoyl having 2 to 5 C atoms.
- Z is preferably --CH 2 CH 2 -- or a single bond. In particularly preferred compounds, Z is a single bond.
- a 1 is preferably trans-1,4-cyclohexylene.
- A is preferably 1,4-phenylene.
- Particularly preferred components of the formula I are those of the subformulae Ia, Ib, Ic and Id: ##STR1##
- the dielectrics of the display elements according to the invention preferably contain 10 to 80%, in particular 20 to 70%, of the total content of compounds of the formula I.
- a further preferred total content of compounds of the formula I is 35 to 69%.
- a 2 and A 3 independently of one another, are each preferably trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl, particularly preferably trans-1,4-cyclohexylene.
- R 3 is preferably straight-chain alkyl, preferably having 2 to 7 C atoms, in which, in addition, one CH 2 group may be replaced by --O-- or --CH ⁇ CH--.
- n-Alkyl is particularly preferred.
- R 4 is preferably straight-chain alkyl, preferably having 2 to 7 C atoms, in which, in addition, one CH 2 group may be replaced by --O-- or --CH ⁇ CH--, or is halogen, CN, NCS or N 3 . Particularly preferred meanings for R 4 are n-alkyl, n-alkoxy, F, CN and NCS.
- Z 2 and Z 3 are preferably each, independently of one another, --CH 2 CH 2 --, --CO--O--, --O--CO-- or a single bond. At least one of the groups Z 2 and Z 3 is preferably a single bond.
- A' is preferably 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene, pyridine-2,5-diyl or pyrimidine-2,5-diyl. Particularly preferred meanings for A' are 1,4-phenylene and 2- or 3-fluoro-1,4-phenylene.
- Particularly preferred components of the formula II are those of the subformulae IIa to IIv: ##STR2##
- subformula IIa, IIc, IIj, IIl, IIm, IIn, IIo, IIp, IIq, IIr and IIs are preferred.
- those of the subformulae IIo and IIp are particularly preferred.
- Particularly preferred components of the formula III are those of the subformulae IIIa, IIIb and IIIc: ##STR3##
- preferred dielectrics contain at least one component of the formula II.
- the dielectrics preferably contain 5 to 50%, in particular 10 to 40%, of the total content of compounds of the formulae II and III. A further preferred total content is 20 to 35%.
- Z 4 and Z 5 are each, independently of one another, preferably --CH 2 CH 2 --, --CO--O--, --O--CO-- or a single bond.
- a 4 and A 5 are preferably trans-1,4-cyclohexylene or 1,4-phenylene.
- R 3 , R 4 , A 2 , A 3 , A', Z 2 and Z 3 have the meanings indicated as preferred in the formulae II and III. (m+n) is preferably 1.
- Particularly preferred compounds of the formula IV are those of the subformulae IVa to IVk: ##STR4##
- those of the subformulae IVa, IVb, IVg, IVh, IVj and IVK (sic), in particular those of the subformula IVa, are particularly preferred.
- the dielectrics preferably contain 0 to 40%, in particular 5 to 30%, of the total content of compounds of the formula IV.
- the content in the dielectrics of compounds which are decidedly positive dielectrically is advantageously 10 to 50%, particularly preferably 20 to 40%.
- any customary dielectrically positive components can be employed.
- the choice of the most highly suitable compounds depends, above all, on the threshold voltage and optical anisotropy desired.
- Dielectrically positive compounds of the formulae II, III and/or IV can be chosen and/or other customary compounds, for example those of the formulae Va to Ve below: ##STR5##
- the voltage in the case of so-called static drive, is switched from 0 volt to a voltage which is, for example, approximately twice to 3 times the threshold voltage. If the threshold is, for example, 2.0 volts, the switching time can be measured on switching from 0 volts to 4-6 volts and back. Under these conditions, the switch-on times are usually somewhat shorter than the switch-off times.
- the voltage is switched from a first voltage below or approximately at the threshold to a second voltage on the increase of the characteristic line. This applies, in particular, in the case of relatively high multiplex ratios and in TFT displays. Under these conditions, the switch-on times, in particular, are very long.
- the voltage in our measurements is switched from a fixed initial voltage of exactly 1.00 volt to a voltage at which 40% of the maximum contrast is achieved (when observed vertically).
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Abstract
Compounds of the formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
in which
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, where two O atoms are not linked directly to one anther, or one of the two groups R1 and R2 is alternatively H,
Z1 is --CH2 --O--, --OCH2 --, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
A is unsubstituted or fluorine-substituted 1,4-phenylene, can be used as components of liquid-crystalline dielectrics containing at least three liquid-crystalline compounds for shortening the switch-on time Ton of electrooptical display elements based on a TN cell on switching the voltage from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line.
Description
This application is a continuation, of application Ser. No. 07/272,831, filed Oct. 17, 1988, which is based on PCT/EP88/00090 filed Feb. 8, 1988, now abandoned.
The invention relates to electrooptical liquid-crystal display elements (LC display elements) based on TN cells having a particularly short switch-on time Ton when switched from a first voltage below or approximately at the threshold voltage to a second voltage which is on the increase of the electrooptical characteristic line. The invention is thus of particular importance in high-multiplex LC display elements and in particular in TFT-addressed LC display elements having a particularly short switch-on time.
For LC display elements, the properties of nematic or nematic cholesteric liquid-crystalline materials to modify their optical properties, such as light absorption, light scattering, birefringence, reflectivity or color are utilized. At the same time, the function of display elements of this type is based, for example, on the phenomena of dynamic scattering and the deformation of allied phases, on the guest-host effect, the Schadt-Helfrich effect in the twisted cell, the SBE effect or the cholesteric-nematic phase transition.
For industrial use of these effects in electronic components, LC phases are required which must satisfy a large number of requirements. Particularly, important here are the chemical resistance to moisture, air and physical influences, such as heat, radiation in the infra-red, visible and ultra-violet region and electrical direct current and alternating current fields. Furthermore, a liquid-crystalline mesophase in a suitable temperature range, low viscosity, an optical anisotropy matched to the layer thickness, low temperature dependence of the threshold voltage, steep gradients of the electrooptical characteristic line and adequate dissolution capacity for pleochroic dyes are required of LC phases which can be used industrially.
In none of the series of compounds having a liquid-crystalline mesophase known hitherto is there a single compound which satisfies all these requirements. Generally, therefore, mixtures of two to 25, preferably three to 18, compounds are prepared in order to obtain substances which can be used as LC phases. However, ideal phases cannot easily be produced in this way since components of high melting and clear points frequently also confer high viscosity on the mixtures. The switching times of the electrooptical display elements produced therewith are thereby altered in an undesired manner.
In order to shorten the switching times, components of low viscosity or glass-transition temperatures and/or particularly advantageous elastic constants are employed in the LC phases known hitherto. However, these phases do not simultaneously satisfy all the abovementioned requirements. In particular, their switch-on time Ton is, as before, still too long for many applications, in particular in LC display elements in which the switchover takes place from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line.
An essential distinction is made in electrooptical liquid-crystal display elements between static drive and multiplex drive. In order to switch on in the case of static drive, the voltage is switched from 0 volts to a voltage approximately at or above the saturation voltage (=the voltage with which 90% of the maximum contrast is obtained). On switching off, the voltage is switched back to 0 volts. In electrooptical liquid-crystal display elements which are driven in "multiplex operation", the voltage is switched from a first voltage V (off) to a second voltage V (on) and back. The ratio between these two voltages is determined by the "multiplex ratio" and the "bias". The absolute values for the two voltages are given by the operating voltage.
N=the number of "multiplex" lines (1/N=multiplex ratio) ##EQU1##
At a multiplex ratio of 1:4 and a bias of 1:3, for example, the V(on):V(off) ratio is 1.73. At an operating voltage of 3 volts, V(on) is 1.73 volts and V(off) is 1.00 volt.
At a multiplex of 1:16 and a bias of 1:5, the V(on):V(off) ratio is, for example, 1.29; at an operating voltage of 5 volts, V(on) is 1.58 volts and V(off) is 1.22 volts.
For a given display element with pre-specified drive, the dielectric is generally selected so that the initial voltage V(off) is just below or in the region of the "threshold voltage" (=voltage for 10% of the maximum contrast) for certain observation angle or for a certain observation angle range. The second voltage V(on) is then on the increase of the characteristic line above the threshold voltage.
In display elements which are intended to display various gray steps (for example video displays), it is necessary for the brightness to be varied as desired in the range from, for example, 10% of maximum brightness up to, for example, 90% of maximum brightness by switching the voltage.
In the case of multiplex drive (in particular also with gray steps) and TFT drive, when switching on and switching off or when switching from one gray step to another gray step, the voltage is switched from below or in the region of the threshold voltage to a second voltage above the threshold voltage in the region of the increase in the characteristic line.
In the case of "static drive", the switch-on times are generally relatively short since the switch-on voltage is very much greater than the saturation voltage.
In the case of multiplex drive and TFT drive, in contrast, the switch-on times, in particular, are usually relatively long.
There is thus still a great demand for liquid-crystalline phases having high clear points, low melting points and very short switch-on times when used in LC display elements in which the voltage is switched from below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line.
The invention has the object of providing LC display elements which have a broad operating temperature range and only have the abovementioned disadvantages to a lesser extent, or not at all.
It has now been found that LC display elements having particularly favorable electrooptical properties, in particular having extremely short switch-on times Ton when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, are obtained when the dielectric contains at least one component of the formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
in which
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, where two O atoms are not linked directly to one another, or one of the two groups R1 and R2 is alternatively H,
Z1 is --CH2 --O--, --OCH2 --, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
A is unsubstituted or fluorine-substituted 1,4-phenylene.
The invention thus relates to a LC display element containing a liquid-crystalline phase described above, in particular an electrooptical display element based on a TN cell having a particularly short switch-on time Ton when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, characterized in that the dielectric simultaneously contains at least one component of the formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
in which
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, where two O atoms are not linked directly to one another, or one of the two groups R1 and R2 is alternatively H,
Z1 is --CH2 --O--, --OCH2 --, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and is unsubstituted or fluorine-substituted 1,4-phenylene,
and at least one component selected from the compounds of the formulae II and III
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --A'--R.sup.4 II
R.sup.3 --A.sup.2 --Z.sup.2 --A'--Z.sup.3 --A.sup.3 --R.sup.4III
in which
R3 is H or alkyl having 1 to 9 C atoms, in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--,
R4 is H, alkyl having 1 to 9 C atoms in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, halogen, CN, NCS or N3,
Z2 and Z3 are each --CH2 CH2 --, --OCH2 --, --CH2 O-- --O--CO--, --CO--O--, or a single bond,
A2 and A3 are each trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S,
A' is unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N.
The invention furthermore relates to an appropriate display element whose dielectric additionally contains at least one component of the formula IV
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --(Z.sup.4 --A.sup.4).sub.m --Z.sup.3 --A'--(Z.sup.5 --A.sup.5).sub.n --R.sup.4 IV
in which
Z4 and Z5 are each --CH2 CH2 --, --OCH2 --, --CH2 O--, --O--CO--, --CO--O-- or a single bond,
A4 and A5 are each trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
m and n are each 0 or 1,
and R3, R4, A2, A3, A, Z2 and Z3 have the meaning given in claim 4, and an appropriate electrooptical display element which is operated in the region of the first transmission minimum according to Gooch-Tarry.
The invention furthermore relates to the use of compounds of the formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
in which
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, where two O atoms are not linked directly to one another, or one of the two groups R1 and R2 is alternatively H,
Z1 is --CH2 --O--, --OCH2 --, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
A is unsubstituted or fluorine-substituted 1,4-phenylene,
as components of liquid-crystalline dielectrics containing at least three liquid-crystalline compounds, for shortening the switch-on time Ton of electrooptical display elements based on a TN cell when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, and to a process for shortening the switch-on time Ton of electrooptical display elements based on a TN cell when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, characterized in that the dielectric contains at least one component of the formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
in which
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, where two O atoms are not linked directly to one another, or one of the two groups R1 and R2 is alternatively H,
Z1 is --CH2 --O--, --OCH2 --, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
A is unsubstituted or fluorine-substituted 1,4-phenylene.
The invention finally relates to a dielectric for use in an electrooptical display element based on a TN cell having a particularly short switch-on time Ton when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, characterized in that it simultaneously contains one component of the formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
in which
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, where two O atoms are not linked directly to one another, or one of the two groups R1 and R2 is alternatively H,
Z1 is --CH2 --O--, --OCH2 --, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
A is unsubstituted or fluorine-substituted 1,4-phenylene, and at least one component selected from the compounds of the formulae II and III
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --Z.sup.3 --A'--R.sup.4II
R.sup.3 --A.sup.2 --Z.sup.2 --A'--Z.sup.3 --A.sup.3 --R.sup.4III
in which
R3 is H or alkyl having 1 to 9 C atoms, in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--,
R4 is H, alkyl having 1 to 9 C atoms in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, halogen, CN, NCS or N3,
Z2 and Z3 are each --CH2 CH2 --, --OCH2 --, --CH2 O-- --O--CO--, --CO--O--, or a single bond,
A2 and A3 are each trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S,
A' is unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
and a corresponding dielectric containing at least one component of the formula IV
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --(Z.sup.4 --A.sup.4).sub.m --Z.sup.3 --A'--(Z.sup.5 --A.sup.5).sub.n --R.sup.4 IV
in which
Z4 and Z5 are each --CH2 CH2 --, --OCH2 --, --CH2 O--, --O--CO--, --CO--O-- or a single bond,
A4 and A5 are each trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
m and n are each 0 or 1,
and R3, R4, A2, A3, A, Z2 and Z3 have the meaning given in claim 4.
The dielectrics may also contain further additives known to those skilled in the art and described in the literature. For example, 0-15% of pleochroic dyes, furthermore conductive salts, for example ethyldimethyldodecylammonium 4-hexoxybenzoate, tetrabutylammonium tetraphenylborate or complex salts of crown ethers (compare, for example, Haller et al., Mol. Cryst. Liq. Cryst. Volume 24, pages 249-258, (1973)) for improving the conductivity, or substances for modifying the dielectric anisotropy, the viscosity and/or the orientation of the nematic phases can be added. Such substances are described, for example, in DE-OS 2,209,127, 2,240,864, 2,321,632, 2,338,281, 2,450,088, 2,637,430 and 2,853,728.
The individual components of the formula I, II, III and IV of the liquid-crystalline phases according to the invention are either known or can easily be derived from the prior art by the relevant person skilled in the art since they are based on standard processes described in the literature.
Corresponding compounds are described, for example, in German Patent Applications 2,636,684, 2,800,553, 2,933,563, 2,933,611, 2,948,836, 3,001,661, 3,102,017, 3,149,139, 3,206,269, 3,139,130, 3,223,637, 3,211,601, 3,317,597, 3,317,921, 3,339,218, 3,401,320, 3,410,734 and 3,545,345, in European Patent Applications 0,019,665, 0,058,512, 0,062,470, 0,084,194, 0,084,974, 0,090,671, 0,094,198, 0,099,099, 0,102,047, 0,119,756, 0,122,389, 0,129,177, 0,167,912 and 0,168,683, in the International Patent Application WO 85/04874, in Japanese Patent Applications 58-126,821-A, 58-177,989-A, 60-161,941-A, 60-161,957-A, 60-222,458-A and 60-239,470-A and in U.S. Pat. No. 4,439,015.
Surprisingly, it has been shown that the dielectrics according to the invention, in particular the combination of components of the formulae I and II and/or III, have significantly shorter switching times (in particular significantly shorter switch-on times) under the specific drive conditions mentioned (that is to say, for example, in TFT or high-multiplex displays) than other dielectrics without this specific substance combination, even if relevant physical properties and measurement conditions (rotational viscosity, elastic constants, the product d×Δn of the layer thickness and the optical anisotropy, and the drive voltage) are virtually identical.
The better switching (switch-on) times of the LC display elements according to the invention are caused not only by better viscosities or more suitable elastic constants. The reason is very probably above all the type of interactions between the LC molecules and the display surfaces. In particular, it can be assumed that the mixtures according to the invention have a greater tilt angle than other comparable mixtures and the switch-on time especially is therefore significantly shorter.
If other compounds which do not meet the criteria mentioned (for example molecules which contain exclusively cyclohexane rings) are added to dielectrics of this type, the switching times are impaired.
In the compounds of the formula I, R1 and R2 are, independently of one another, preferably alkyl in which, in addition, a CH2 group (which is not linked directly to --O-- or --A1 --) may be replaced by --O-- or --CH═CH--. Straight-chain alkyl groups having 1 to 5 C atoms are particularly preferred. Compounds of the formula I in which R2 is alkanoyl are furthermore preferred. R2 is then preferably straight-chain alkanoyl having 2 to 5 C atoms. Z is preferably --CH2 CH2 -- or a single bond. In particularly preferred compounds, Z is a single bond. A1 is preferably trans-1,4-cyclohexylene. A is preferably 1,4-phenylene. Particularly preferred components of the formula I are those of the subformulae Ia, Ib, Ic and Id: ##STR1##
Compounds of the subformula Ia are particularly preferred.
The dielectrics of the display elements according to the invention preferably contain 10 to 80%, in particular 20 to 70%, of the total content of compounds of the formula I. A further preferred total content of compounds of the formula I is 35 to 69%.
In the compounds of the formulae II and III, A2 and A3, independently of one another, are each preferably trans-1,4-cyclohexylene or trans-1,3-dioxane-2,5-diyl, particularly preferably trans-1,4-cyclohexylene. R3 is preferably straight-chain alkyl, preferably having 2 to 7 C atoms, in which, in addition, one CH2 group may be replaced by --O-- or --CH═CH--. n-Alkyl is particularly preferred. R4 is preferably straight-chain alkyl, preferably having 2 to 7 C atoms, in which, in addition, one CH2 group may be replaced by --O-- or --CH═CH--, or is halogen, CN, NCS or N3. Particularly preferred meanings for R4 are n-alkyl, n-alkoxy, F, CN and NCS. Z2 and Z3 are preferably each, independently of one another, --CH2 CH2 --, --CO--O--, --O--CO-- or a single bond. At least one of the groups Z2 and Z3 is preferably a single bond.
A' is preferably 1,4-phenylene, 2- or 3-fluoro-1,4-phenylene, pyridine-2,5-diyl or pyrimidine-2,5-diyl. Particularly preferred meanings for A' are 1,4-phenylene and 2- or 3-fluoro-1,4-phenylene.
Particularly preferred components of the formula II are those of the subformulae IIa to IIv: ##STR2##
Of these, those of the subformula IIa, IIc, IIj, IIl, IIm, IIn, IIo, IIp, IIq, IIr and IIs are preferred. Those of the subformulae IIo and IIp are particularly preferred.
Particularly preferred components of the formula III are those of the subformulae IIIa, IIIb and IIIc: ##STR3##
Of these, those of the subformulae IIIa and IIIc, in particular IIIa, are preferred.
Besides components of the formula I, preferred dielectrics contain at least one component of the formula II.
The dielectrics preferably contain 5 to 50%, in particular 10 to 40%, of the total content of compounds of the formulae II and III. A further preferred total content is 20 to 35%.
In the compounds of the formula IV, Z4 and Z5 are each, independently of one another, preferably --CH2 CH2 --, --CO--O--, --O--CO-- or a single bond. A4 and A5 are preferably trans-1,4-cyclohexylene or 1,4-phenylene. R3, R4, A2, A3, A', Z2 and Z3 have the meanings indicated as preferred in the formulae II and III. (m+n) is preferably 1.
Particularly preferred compounds of the formula IV are those of the subformulae IVa to IVk: ##STR4##
Of these, those of the subformulae IVa, IVb, IVg, IVh, IVj and IVK (sic), in particular those of the subformula IVa, are particularly preferred.
The dielectrics preferably contain 0 to 40%, in particular 5 to 30%, of the total content of compounds of the formula IV.
The content in the dielectrics of compounds which are decidedly positive dielectrically is advantageously 10 to 50%, particularly preferably 20 to 40%. In principle, any customary dielectrically positive components can be employed. The choice of the most highly suitable compounds depends, above all, on the threshold voltage and optical anisotropy desired. Dielectrically positive compounds of the formulae II, III and/or IV can be chosen and/or other customary compounds, for example those of the formulae Va to Ve below: ##STR5##
The examples below are intended to illustrate the invention without representing a limitation.
The symbols have the following meanings:
______________________________________
S-N smectic-nematic phase transition temperature,
in degrees Celsius,
c.p. clear point, in degrees Celsius,
visc. viscosity at 20° (mPa · s),
thresh. threshold voltage of a TN cell at 20°, observa-
tion angle 0° (vertical) and a contrast of 10%.
T.sub.on,
switch-on or switch-off time in msec.
T.sub.off
K.sub.3 /K.sub.1
ratio between the elastic constants of bending
and stretching
n birefringence
______________________________________
Above and below all temperatures are given in °C. The percentages are by weight.
Procedure for measuring the switching time:
If the switching times of liquid crystals in displays are to be measured, the voltage, in the case of so-called static drive, is switched from 0 volt to a voltage which is, for example, approximately twice to 3 times the threshold voltage. If the threshold is, for example, 2.0 volts, the switching time can be measured on switching from 0 volts to 4-6 volts and back. Under these conditions, the switch-on times are usually somewhat shorter than the switch-off times.
In the case of multiplex drive, however, the voltage is switched from a first voltage below or approximately at the threshold to a second voltage on the increase of the characteristic line. This applies, in particular, in the case of relatively high multiplex ratios and in TFT displays. Under these conditions, the switch-on times, in particular, are very long.
In order to simulate these conditions, the voltage in our measurements is switched from a fixed initial voltage of exactly 1.00 volt to a voltage at which 40% of the maximum contrast is achieved (when observed vertically).
The investigations were carried out on mixtures for the "first minimum" according to Gooch and Tarry. The product of the layer thickness and the birefringence was therefore in the region of about 0.5.
A mixture comprising
______________________________________
28% trans-1-p-methoxyphenyl-4-propylcyclohexane,
23% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
18% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl,
7% trans,trans-4-(2-p-cyanophenyl-ethyl)-4'-ethyl-
bicyclohexyl,
7% trans,trans-4-(2-p-cyanophenyl-ethyl)-4'-propyl-
bicyclohexyl,
and
6% trans,trans-4-(2-p-cyanophenyl-ethyl)-4'-pentyl-
bicyclohexyl,
______________________________________
exhibits c.p. 76.3°, Δn 0.1004, thresh. 2.6 V, Ton 120 msec and Toff 15 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
22% trans-1-p-methoxyphenyl-4-propylcyclohexane,
16% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
11% trans-1-p-butoxyphenyl-4-propylcyclohexane,
10% trans,trans-4-(2-p-fluorophenyl-ethyl)-4'-pentyl-
bicyclohexyl,
10% trans,trans-4-(2-p-propylphenyl-ethyl)-4'-propyl-
bicyclohexyl,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl
and
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 71°, Δn 0.1017, thresh. 2.1 V, Ton 86 msec and Toff 15 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
10% p-propylphenyl trans,trans-4-propyl-bicyclohexyl-
4'-carboxylate,
10% p-pentylphenyl trans,trans-4-propyl-bicyclohexyl-
4'-carboxylate,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl
and
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 79.5°, Δn 0.1029, thresh. 2.13 V, Ton 98 msec, Toff 14 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
10% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate,
10% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl
and
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 80.3°, Δn 0.1003, thresh. 2.2 V, Ton 127 msec and Toff 16 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
22% trans-1-p-methoxyphenyl-4-propylcyclohexane,
16% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
11% trans-1-p-butyxophenyl-4-propylcyclohexane,
10% trans,trans-4-(2-p-propylphenyl-ethyl)-4'-propyl-
bicyclohexyl,
10% trans,trans-4-(2-p-propylphenyl-ethyl)-4'-pentyl-
bicyclohexyl,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl
and
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 71.8°, Δn 0.1030, thresh. 2.16 V, Ton 107 msec and Toff 16 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
22% trans-1-p-methoxyphenyl-4-propylcyclohexane,
16% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
11% trans-1-p-butoxyphenyl-4-propylcyclohexane,
20% trans,trans-4-(2-p-fluorophenyl-ethyl)-4'-pentyl-
bicyclohexyl,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-bisphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl
and
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 72.0°, Δn 0.1000, thresh. 2.13 V, Ton 126 msec and Toff 19 msec.
A mixture comprising
______________________________________
12% p-trans-4-propylcyclohexyl-benzonitrile,
8% p-trans-4-butylcyclohexyl-benzonitrile,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
13% trans-1-p-butoxyphenyl-4-butylcyclohexane,
8% trans-1-p-ethoxyphenyl-4-butylcyclohexane,
9% trans-1-p-methoxyphenyl-4-pentylcyclohexane,
5% trans-1-p-ethoxyphenyl-4-pentylcyclohexane,
5% p-propylphenyl trans,trans-4-propyl-bicyclohexyl-
4'-carboxylate,
5% p-pentylphenyl trans,trans-4-propyl-bicyclohexyl-
4'-carboxylate,
5% p-propylphenyl trans,trans-4-butyl-bicyclohexyl-
4'-carboxylate,
5% p-pentylphenyl trans,trans-4-butyl-bicyclohexyl-
4'-carboxylate,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-trans-4-pentylcyclohexyl)-biphenyl
and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 81°, Δn 0.1007, thresh. 2.3 V, Ton 108 msec. and Toff 16 msec.
A mixture comprising
______________________________________
15% p-trans-4-propylcyclohexyl-benzonitrile,
10% p-trans-4-butylcyclohexyl-benzonitrile,
15% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
10% trans-1-p-butoxyphenyl-4-propylcyclohexane,
20% trans,trans-4-(2-p-propylphenyl-ethyl)-4'-propyl-
bicyclohexyl
and
15% trans,trans-4-(2-p-propylphenyl-ethyl)-4'-pentyl-
bicyclohexyl
______________________________________
exhibits c.p. 64.8°, Δn 0.0940, thresh. 1.95 V, Ton 119 msec and Toff msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
15% trans-1-p-methoxy-4-propylcyclohexane,
10% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
10% trans-1-p-butoxyphenyl-4-propylcyclohexane,
14% trans,trans-4-propoxy-4'-propyl-bicyclohexane,
10% p-propylphenyl trans,trans-4-propyl-bicyclohexyl-
4'-carboxylate,
10% p-pentylphenyl trans,trans-4-propyl-bicyclohexyl-
4'-carboxylate,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl
and
6% 4-(trans-4-pentylcyclohexyl)-4'-)trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 81.7°, Δn 0.0975, thresh. 2.15 V, Ton 122 msec and Toff 18 msec.
A mixture comprising
______________________________________
15% p-trans-4-propylcyclohexyl-benzonitrile,
5% 4-ethyl-4'-cyanobiphenyl,
5% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
13% trans-1-p-methoxyphenyl-4-propylcyclohexane,
10% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
10% trans-1-p-butoxyphenyl-4-propylcyclohexane,
5% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-propylcyclohexyl)-2-fluorobi-
phenyl,
5% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-pentylcyclohexyl)-2-fluorobi-
phenyl,
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-2-fluorobiphenyl
______________________________________
exhibits c.p. 88°, Δn 0.1378 and favorable switching times.
A mixture comprising
______________________________________
17% p-trans-4-propylcyclohexyl-benzonitrile,
4% 4-ethyl-4'-cyanobiphenyl,
4% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
13% trans-1-p-methoxyphenyl-4-propylcyclohexane,
10% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
9% trans-1-p-butoxyphenyl-4-propylcyclohexane,
5% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-propylcyclohexyl)-2-fluorobiphenyl,
5% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-pentylcyclohexyl)-2-fluoro-
biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-2-fluorobiphenyl
______________________________________
exhibits c.p. 91°, Δn 0.1393, thresh. 1.9 V and favorable switching times.
A mixture comprising
______________________________________
4% 3-fluoro-4-cyanophenyl p-ethylbenzoate,
5% 3-fluoro-4-cyanophenyl p-propylbenzoate,
5% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-(trans-4-propylcyclohexyl)-
benzoate,
4% 3-fluoro-4-cyanophenyl p-(trans-4-pentylcyclohexyl)-
benzoate,
16% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
15% trans-1-p-butoxyphenyl-4-propylcyclohexane,
12% 4-ethyl-4'-(trans-4-propylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-propylcyclohexyl)-2-fluorobiphenyl,
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-2-fluorobiphenyl
______________________________________
exhibits c.p. 96°, Δn 0.1317, thresh. 1.9 V and favorable switching times.
A mixture comprising
______________________________________
5% 3-fluoro-4-cyanophenyl p-ethylbenzoate,
5% 3-fluoro-4-cyanophenyl p-propylbenzoate,
5% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-(trans-4-propylcyclohexyl)-
benzoate,
4% 3-fluoro-4-cyanophenyl p-(trans-4-pentylcyclohexyl)-
benzoate,
17% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
15% trans-1-p-butoxyphenyl-4-propylcyclohexane,
11% 4-ethyl-4'-(trans-4-propylcyclohexyl)-biphenyl,
4% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-propylcyclohexyl)-2-fluorobiphenyl,
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-2-fluorobiphenyl
______________________________________
exhibits c.p. 91°, Δn 0.1317, thresh. 1.8 V and favorable switching times.
A mixture comprising
______________________________________
9% p-trans-4-propylcyclohexyl-benzonitrile,
9% 4-ethyl-4'-cyanobiphenyl,
7% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
16% trans-1-p-methoxyphenyl-4-propylcyclohexane,
4% p-propylphenyl trans-4-(trans-4-propylcyclo-
hexyl)-cyclohexanecarboxylate,
4% p-pentylphenyl trans-4-(trans-4-propylcyclo-
hexyl)-cyclohexane-carboxylate,
4% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
4% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% 1-[trans-4-(trans-4-pentylcyclohexyl-cyclohexyl]-
2-(p-propylphenyl)-ethane,
11% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate and
10% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate
______________________________________
exhibits c.p. 90° and favorable switching times.
A mixture comprising
______________________________________
9% p-trans-4-propylcyclohexyl-benzonitrile,
9% 4-ethyl-4'-cyanobiphenyl,
7% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
16% trans-1-p-methoxyphenyl-4-propylcyclohexane,
3% p-propylphenyl trans-4-(trans-4-propylcyclo-
hexyl)-cyclohexanecarboxylate,
3% p-pentylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
3% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
3% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
6% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane
5% 1-[trans-4-(trans-4-)pentylcyclohexyl)-cyclohexyl]-2-(p-
propylphenyl)-ethane,
12% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate and
12% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate
______________________________________
exhibits c.p. 91° and favorable switching times.
A mixture comprising
______________________________________
4% 3-fluoro-4-cyanophenyl p-(trans-4-propylcyclohexyl)-
benzoate,
4% 3-fluoro-4-cyanophenyl p-(trans-4-pentylcyclohexyl)-
benzoate,
14% trans-1-p-propylphenyl-4-pentylcyclohexane,
5% 3-fluoro-4-cyanophenyl p-propylbenzoate,
5% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
5% 3-fluoro-4-cyanophenyl p-ethylbenzoate,
18% trans-1-p-methoxyphenyl-4-propylcyclohexane,
5% p-propylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
5% 1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
8% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate, and
7% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate
______________________________________
exhibits c.p. 93° and favorable switching times.
A mixture comprising
______________________________________
11% p-trans-4-propylcyclohexyl-benzonitrile,
8% 4-ethyl-4'-cyanobiphenyl,
6% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
16% trans-1-p-methoxyphenyl-4-propylcyclohexane,
5% p-propylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
5% 1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
9% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate, and
8% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate
______________________________________
exhibits c.p. 91° and favorable switching times.
A mixture comprising
______________________________________
12% p-trans-4-propylcyclohexyl-benzonitrile,
8% p-trans-4-butylcyclohexyl-benzonitrile,
7% 4-ethyl-4'-cyanobiphenyl,
7% trans-1-p-butoxyphenyl-4-propylcyclohexane,
7% trans-1-p-ethoxyphenyl-4-butylcyclohexane,
7% trans-1-p-methoxyphenyl-4-pentylcyclohexane,
10% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
5% p-propylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
20(p-propylphenyl)-ethane,
4% 1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
4% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate,
4% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl)-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 90° and favorable switching times.
A mixture comprising
______________________________________
11% p-trans-4-propylcyclohexyl-benzonitrile,
9% 4-ethyl-4'-cyanobiphenyl,
6% 4-propyl-4'-cyanobiphenyl,
6% 4-butyl-4'-cyanobiphenyl,
13% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
10% trans-1-p-butoxyphenyl-4-propylcyclohexane,
5% p-propylphenyl trans-4-(trans-4-propylcyclo-
hexyl)-cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyhclohexanecarboxylate,
4% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)ethane,
4% 1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
6% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate,
6% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate and
5% 4-trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 95° and favorable switching times.
A mixture comprising
______________________________________
9% p-trans-4-propylcyclohexyl-benzonitrile,
9% 4-ethyl-4'-cyanobiphenyl,
7% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
16% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
5% p-propylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
5% 1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
9% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate and
8% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate
______________________________________
exhibits c.p. 94° and favorable switching times.
A mixture comprising
______________________________________
9% p-trans-4-propylcyclohexyl-benzonitrile,
9% 4-ethyl-4'-cyanobiphenyl,
7% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
16% trans-1-p-methoxyphenyl-4-propylcyclohexane,
5% p-propylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-propylcyclohexyl)-
cyclohexanecarboxylate,
5% p-propylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% p-pentylphenyl trans-4-(trans-4-butylcyclohexyl)-
cyclohexanecarboxylate,
5% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
5% 1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
9% p-trans-4-propylcyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate and
8% p-trans-4-propylcyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate
______________________________________
exhibits c.p. 90° and favorable switching times.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl,
10% p-fluorophenyl trans,trans-4-propylcyclohexyl-
cyclohexane-4'-carboxylate and
10% p-fluorophenyl trans,trans-4-pentylcyclohexyl-
cyclohexane-4'-carboxylate
______________________________________
exhibits c.p. 77°; Δn 0.1020; thresh. 1.83 V; Ton 104 msec and Toff 18 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
22% trans-1-p-methoxyphenyl-4-propylcyclohexane,
16% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
11% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl,
10% trans,trans-4-pentyl-4'-(5-propylpyridimin-2-
yl)-cyclohexylcyclohexane and
10% trans,trans-4-butyl-4'-(5-propylpyridimin-2-
yl)-cyclohexylcyclohexane
______________________________________
exhibits c.p. 73°; Δn 0.1025; thresh. 2.24 V; Ton 35 msec and Toff 23 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcylohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
20% trans,trans,-4-butyl-4'-(5-heptylpyridimin-2-yl)-
cyclohexylcyclohexane
______________________________________
exhibits c.p. 70°; Δn 0.1000; thresh. 2.10 V; Ton 158 msec and Toff 17 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
20% trans-5-pentyl-2-[trans-4-(p-pentylphenyl)-
cyclohexyl-1,3-dioxane
______________________________________
exhibits c.p. 65°; Δn 0.1001; thresh. 1.88 V; Ton 113 msec and Toff 22 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl,
10% [p-(trans-4-propyl-cyclohexyl)-ethyl]-phenyl
trans-4-[trans-(4-pentylcyclohexyl)-ethyl]-cyclo-
hexanecarboxylate and
10% [p-(trans-4-pentyl-cyclohexyl)-ethyl]-phenyl
trans-4-[trans-(4-pentylcyclohexyl)-ethyl]-cyclo-
hexanecarboxylate
______________________________________
exhibits c.p. 88°; Δn 0.1054; thresh. 2.28 V; Ton 133 msec and Toff 21 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
28% trans-1-p-methoxyphenyl-4-propylcyclohexane,
23% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
18% trans-1-p-butoxyphenyl-4-propylcyclohexane and
11% 2-[trans-4-(p-pentylphenyl)-cyclohexyl]-5-(trans-
4-pentylcyclohexyl)-trans-1,3-dioxane
______________________________________
exhibits c.p. 42°; Δn 0.0861; thresh. 2.06 V; Ton 153 msec and Toff 28 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-bisphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
20% 1-[trans-4-propylcyclohexyl)-cyclohexyl]-
2-3-fluoro-4-cyanophenyl)-ethane
______________________________________
exhibits c.p. 75°; Δn 0.1100; thresh. 1.52 V; Ton 80 msec and Toff 26 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
20% p-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
benzene
______________________________________
exhibits c.p. 63°; Δn 0.0996; thresh. 2.05 V; Ton 110 msec and Toff 15 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-(bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
20% 1-[trans-4-(trans-4-pentylcyclohexyl)-cyclohexyl]-
2-(p-methoxyphenyl)-ethane
______________________________________
exhibits favorable switching times.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
20% trans-1-p-methoxyphenyl-4-propylcyclohexane,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
14% trans-1-p-butoxyphenyl-4-propylcyclohexane,
3% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
2% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl,
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
20% p-(trans-4-propylcyclohexyl)-phenyl trans,trans-
4-propylcyclohexylcyclohexane-4'-carboxylate
______________________________________
exhibits c.p. 98°; Δn 0.1082; thresh. 2.45 V; Ton 115 msec and Toff 13 msec.
A mixture comprising
______________________________________
20% p-trans-4-propylcyclohexyl-benzonitrile,
21% trans-1-p-methoxyphenyl-4-propylcyclohexane,
16% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
15% trans-1-p-butoxyphenyl-4-propylcyclohexane,
20% p-(trans-4-propylcyclohexyl)-phenyl trans,trans-
4-propylcyclohexylcyclohexane-4'-carboxylate and
8% p-pentylphenyl trans,trans-4-propylcyclohexyl-
cyclohexane-4'-carboxylate
______________________________________
exhibits c.p. 82°; Δn 0.0982; thresh. 2.25 V; Ton 128 msec and Toff 18 msec.
A mixture comprising
______________________________________
11% p-trans-4-propylcyclohexyl-benzonitrile,
8% 4-ethyl-4'-cyanobiphenyl,
6% 4-propyl-4'-cyanobiphenyl,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
4% 3-fluoro-4-cyanophenyl p-pentylbenzoate,
4% 3-fluoro-4-cyanophenyl p-heptylbenzoate,
19% trans-1-p-methoxyphenyl-4-propylcyclohexane,
5% p-propylphenyl trans,trans-4-propylcyclohexyl-
cyclohexne-4'-carboxylate,
4% p-pentylphenyl trans,trans-4-propylcyclohexyl-
cyclohexane-4'-carboxylate,
4% p-pentylphenyl trans,trans-4-butylcyclohexyl-
cyclohexane-4'-carboxylate,
4% p-propylphenyl trans,trans-4-butylcyclohexyl-
cyclohexane-4'-carboxylate,
5% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-propylphenyl)-ethane,
5% 1-[trans-4-(trans-4-propylcyclohexyl)-cyclohexyl]-
2-(p-pentylphenyl)-ethane,
6% p-trans-4-propyl-cyclohexylphenyl trans-4-butyl-
cyclohexanecarboxylate,
5% p-trans-4-propyl-cyclohexylphenyl trans-4-pentyl-
cyclohexanecarboxylate and
6% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-2-fluorobiphenyl
______________________________________
exhibits c.p. 90°; Δn 0.1259; thresh. 1.8 V and favorable switching times.
A mixture comprising
______________________________________
12% p-trans-4-propylcyclohexyl-benzonitrile,
8% p-trans-4-butylcyclohexyl-benzonitrile,
13% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
11% trans-1-p-butoxyphenyl-4-propylcyclohexane,
8% trans-1-p-ethoxyphenyl-4-butylcyclohexane,
9% trans-1-p-methoxyphenyl-4-pentylcyclohexane,
5% trans-1-p-ethoxyphenyl-4-pentylcyclohexane,
5% p-propylphenyl trans,trans-4-propylcyclohexyl-
cyclohexane-4'-carboxylate,
5% p-pentylphenyl trans,trans-4-propylcyclohexyl-
cyclohexane-4'-carboxylate,
5% p-pentylphenyl trans,trans-4-butylcyclohexylcyclo-
hexane-4'-carboxylate,
5% p-propylphenyl trans,trans-4-butylcyclohexyl-
cyclohexane-4'carboxylate,
4% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 91°; Δn 0.1045, thresh. 2.2 V and favorable switching times.
A mixture comprising
______________________________________
5% 3-fluoro-4-cyanophenyl p-ethylbenzoate,
4% 3-fluoro-4-cyanophenyl p-propylbenzoate,
15% trans-1-p-ethoxyphenyl-4-propylcyclohexane,
13% trans-1-p-butoxyphenyl-4-propylcyclohexane,
10% trans-1-p-ethoxyphenyl-4-butylcyclohexane,
9% trans-1-p-methoxyphenyl-4-pentylcyclohexane,
10% trans,trans-4-propyl-4'-propoxycyclohexylcyclo-
hexane,
5% p-propylphenyl trans,trans-4-propylcyclohexyl-
cyclohexane-4'-carboxylate,
5% p-pentylphenyl trans,trans-4-propylcyclohexyl-
cyclohexane-4'-carboxylate,
5% p-pentylphenyl trans,trans-4-butylcyclohexyl-
cyclohexane-4'-carboxylate,
5% p-propylphenyl trans,trans-4-butylcyclohexyl-
cyclohexane-4'-carboxylate,
4% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
5% 4,4'-bis-(trans-4-pentylcyclohexyl)-biphenyl and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl
______________________________________
exhibits c.p. 90°, Δn 0.1012, thresh. 2.6 V and favorable switching times.
A mixture comprising
______________________________________
15% p-trans-4-propylcyclohexyl-benzonitrile,
10% p-trans-4-butylcyclohexyl-benzonitrile,
11% trans-1-p-ethoxyphenyl-4-propylchclohexane,
6% trans-1-p-butoxyphenyl-4-propylchclohexane,
14% trans,trans-4-propyl-4'-propoxycyclohexylcyclohexane,
6% trans,trans-4-pentyl-4'-methoxycyclohexylcyclohexane,
12% trans,trans-4-pentyl-4'-ethoxycyclohexylcyclohexane,
4% 4,4'-bis-(trans-4-propylcyclohexyl)-biphenyl,
4% 4,4'-bis-(trans-4-propylcyclohexyl)-2-fluoro-
biphenyl,
4% 4,4'-bis-(trans-4-pentylcyclohexyl)-2-fluorophenyl,
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl)-biphenyl and
5% 4-(trans-4-pentylcyclohexyl)-4'-(trans-4-propyl-
cyclohexyl-2-fluorobiphenyl
______________________________________
exhibits c.p. 90°, Δn 0.1003, thresh. 2.4 V and favorable switching times.
Claims (13)
1. A TFT-addressed electrooptical LC display element containing a dielectric with a positive dielectric anisotropy and being based on a TN cell having a short switch-on time Ton when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, said dielectric consisting essentially of at least one component of formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
wherein
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --CH═CH--, or one of the two groups R1 and R2 is H, and R2 may be C1-5 -straight chain alkanoyl,
Z1 is --CH2 --O--, --OCH2, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
A is unsubstituted or fluorine-substituted 1,4-phenylene,
at least one component of formula II
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --Z.sup.3 --A'--R.sup.4II
wherein
R3 is H or alkyl having 1 to 9 C atoms, in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--,
R4 is H, alkyl having 1 to 9 C atoms in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--, halogen, NCS or N3,
Z2 and Z3 are each --CH2 CH2 --, --OCH2 --, --CH2 O--, --O--CO--, --CO--O--, or a single bond,
A2 and A3 are each trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S,
optionally a component of formula IV
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --(Z.sup.4 --A.sup.4).sub.m --Z.sup.3 --A'--(Z.sup.5 --A.sup.5).sub.n --R.sup.4 IV
wherein
Z4 and Z5 are each --CH2 CH2 --, --OCH2 --, --CH2 O--, --O--CO--, --CO--O-- or a single bond,
A4 and A5 are each trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
m and n are each 0 or 1 and (m+n) is 1,
A' is unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
and R3, R4, A2, A3, Z2 and Z3 have the meaning given above.
2. A display element according to claim 1, wherein the dielectric contains one or more compounds selected from the group consisting of compounds of the formulae Ia to Id: ##STR6## wherein alkyl is in each case a straight-chain alkyl group having 1 to 5 C atoms.
3. A display element according to claim 1, wherein the dielectric contains one or more compounds selected from the group consisting of compounds of formulae IIa to IIv: ##STR7## wherein alkyl is in each case a straight-chain alkyl group having 1 to 5 C atoms.
4. A display element according to claim 1, wherein, in addition to compounds of formula I, II and optionally IV, the dielectric contains one or more compounds selected from the group consisting of compounds of formulae IIIa to IIIc: ##STR8## wherein alkyl is in each case a straight-chain alkyl group having 1 to 5 C atoms.
5. A display element according to claim 1, wherein the dielectric contains one or more compounds selected from the group consisting of compounds of formulae ##STR9## wherein alkyl is in each case a straight-chain alkyl group having 1 to 5 C atoms.
6. A display element according to claim 1, wherein the dielectric contains one or more compounds selected from the group consisting of compounds of formulae Va to Ve in an amount not more than 40%: ##STR10## wherein alkyl is in each case a straight-chain alkyl group having 1 to 5 C atoms.
7. An electrooptical display element according to claim 1, wherein operation is in the first transition minimum according to Gooch-Tarry.
8. A display element according to claim 1, wherein R1 and R2 are each independently alkyl in which a CH2 group not linked directly to --O-- or --A1 -- may be replaced by --O-- or --CH═CH--.
9. A display element according to claim 1, wherein R1 and R2 are each independently straight-chain C1-5 -alkyl.
10. A display element according to claim 1, wherein R2 is straight-chain C1-5 -alkanoyl.
11. A display element according to claim 1, wherein R2 is straight-chain C2-5 -alkanoyl.
12. A display element according to claim 1, wherein, in addition to compound of formula I, II and optionally IV, the dielectric contains at least one of ##STR11##
13. A process for shortening the switch-on time Ton of TFT-addressed electrooptical LC display elements based on a TN cell when the voltage is switched from a first voltage below or approximately at the threshold voltage to a second voltage on the increase of the electrooptical characteristic line, comprising using in the dielectric at least one component of the formula I
R.sup.1 --A.sup.1 --Z.sup.1 --A--O--R.sup.2
wherein
R1 and R2, independently of one another, are each alkyl having 1 to 9 C atoms, in which, in addition, one or two CH2 groups may be replaced by --CH═CH, or one of the two groups R1 and R2 is H, and R2 may be C1-5 -straight-chain alkanoyl,
Z1 is --CH2 --O--, --OCH2 --, --CH2 CH2 -- or a single bond,
A1 is trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S, or 1,4-cyclohexenylene, and
A is unsubstituted or fluorine-substituted 1,4-phenylene, and
at least one component of formula II
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --A'--R.sup.4 II
wherein
R3 is H or alkyl having 1 to 9 C atoms, in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH--,
R4 is H, alkyl having 1 to 9 C atoms in which, in addition, one or two nonadjacent CH2 groups may be replaced by --O--, --CO--, --O--CO--, --CO--O-- and/or --CH═CH, halogen, NCS or N3,
Z2 and Z3 are each --CH2 CH2 --, --OCH2 --CH2 O--, --O--CO--, --CO--O--, or a single bond,
A2 and A3 are each trans-1,4-cyclohexylene in which, in addition, one or two nonadjacent CH2 groups may be replaced by O and/or S,
optionally a component of formula IV
R.sup.3 --A.sup.2 --Z.sup.2 --A.sup.3 --(Z.sup.4 --A.sup.4).sub.m --Z.sup.3 --A'--(Z.sup.5 --A.sup.5).sub.n --R.sup.4 IV
wherein
Z4 and Z5 are each --CH2 CH2 --, --OCH2 --CH2 O--, --O--CO--, --CO--O-- or a single bond,
A4 and A5 are each trans-1,4-cyclohexylene or unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N,
A' is unsubstituted or fluorine-substituted 1,4-phenylene in which, in addition, one or two CH groups may be replaced by N, and
m and n are each 0 or 1 and (m+n) is 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US07/815,832 US5288427A (en) | 1987-02-18 | 1991-12-24 | Electrooptical display element |
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE3705071 | 1987-02-18 | ||
| DE19873705071 DE3705071A1 (en) | 1987-02-18 | 1987-02-18 | ELECTROOPTIC DISPLAY ELEMENT |
| PCT/EP1988/000090 WO1988006178A1 (en) | 1987-02-18 | 1988-02-08 | Electro-optical display element |
| US27283188A | 1988-10-17 | 1988-10-17 | |
| US07/815,832 US5288427A (en) | 1987-02-18 | 1991-12-24 | Electrooptical display element |
Related Parent Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US27283188A Continuation | 1987-02-18 | 1988-10-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US5288427A true US5288427A (en) | 1994-02-22 |
Family
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US07/815,832 Expired - Lifetime US5288427A (en) | 1987-02-18 | 1991-12-24 | Electrooptical display element |
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| Country | Link |
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| US (1) | US5288427A (en) |
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| US5397505A (en) * | 1990-10-02 | 1995-03-14 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Liquid crystalline medium |
| US5519525A (en) * | 1988-10-20 | 1996-05-21 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Matrix liquid crystal display |
| US5589103A (en) * | 1993-01-08 | 1996-12-31 | Canon Kabushiki Kaisha | Mesomorphic compound, liquid crystal composition containing same, and liquid crystal device using same |
| US5781263A (en) * | 1996-03-14 | 1998-07-14 | Optrex Corporation | Liquid crystal display device wherein driving frequency is 200 or less and 50% threshold voltage is 1.5 V or less |
| US5779933A (en) * | 1995-04-25 | 1998-07-14 | Chisso Corporation | Liquid crystal composition and liquid crystal display element |
| US5876626A (en) * | 1988-10-20 | 1999-03-02 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Supertwist liquid crystal display |
| US6004479A (en) * | 1988-07-13 | 1999-12-21 | Merck Kgaa | Matrix liquid crystal display |
| US20040033589A1 (en) * | 2000-10-20 | 2004-02-19 | O'brien John Anthony | Biolistic device |
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|---|---|---|---|---|
| US6004479A (en) * | 1988-07-13 | 1999-12-21 | Merck Kgaa | Matrix liquid crystal display |
| US5519525A (en) * | 1988-10-20 | 1996-05-21 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Matrix liquid crystal display |
| US5876626A (en) * | 1988-10-20 | 1999-03-02 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Supertwist liquid crystal display |
| US6562419B1 (en) | 1988-10-20 | 2003-05-13 | Merck Patent Gesellschaft Mit Beschrankter Haftung | Matrix liquid crystal display |
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| US5589103A (en) * | 1993-01-08 | 1996-12-31 | Canon Kabushiki Kaisha | Mesomorphic compound, liquid crystal composition containing same, and liquid crystal device using same |
| US5779933A (en) * | 1995-04-25 | 1998-07-14 | Chisso Corporation | Liquid crystal composition and liquid crystal display element |
| US5781263A (en) * | 1996-03-14 | 1998-07-14 | Optrex Corporation | Liquid crystal display device wherein driving frequency is 200 or less and 50% threshold voltage is 1.5 V or less |
| US20040033589A1 (en) * | 2000-10-20 | 2004-02-19 | O'brien John Anthony | Biolistic device |
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